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Hydrochloric Acid → N-(m-iodobenzoyl)-1,3,4,6-tetra-O-acetyl-D-glucosamine

HRID 1086976
Notes
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Reaction equation

HRID 1086976 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.S(Cl)(Cl)=O.[C:15]([O:18][CH:19]1[O:33][C@H:32]([CH2:34][O:35][C:36](=[O:38])[CH3:37])[C@@H:27]([O:28][C:29](=[O:31])[CH3:30])[C@H:22]([O:23][C:24](=[O:26])[CH3:25])[C@H:20]1[NH2:21])(=[O:17])[CH3:16].Cl>C1C=CC=CC=1.N1C=CC=CC=1>[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH:21][C@@H:20]1[C@@H:22]([O:23][C:24](=[O:26])[CH3:25])[C@H:27]([O:28][C:29](=[O:31])[CH3:30])[C@@H:32]([CH2:34][O:35][C:36](=[O:38])[CH3:37])[O:33][CH:19]1[O:18][C:15](=[O:17])[CH3:16])=[O:7]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 120603-Iodobenzoic acidHCID 24386Thionyl ChlorideHCID 13059363glucosamine tetra-O-acetate

Product 1

HCID 86744916N-(m-iodobenzoyl)-1,3,4,6-tetra-O-acetyl-D-glucosamineYield 45.1%

Reagents, catalysts & solvents 2

HCID 241
Benzene
Solvent
2×
HCID 1049PyridineSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of m-iodobenzoic acid (1.6 g; 6.45×10-3 mol) and thionyl chloride (10 ml) was stirred at 65° C. for 24 hours, benzene was added thereto, and excessive thionyl chloride was removed by distillation under reduced pressure. The thus prepared m-iodobenzoyl chloride was dissolved in benzene (2 ml), and a solution of 1,3,4,6-tetra-O-acetyl-D-glucosamine (2 g; 5.76×10-3 mol) in benzene (10 ml) and pyridine (2 ml) was added thereto, followed by stirring for 48 hours. The resulting mixture was neutralized with 0.1N hydrochloric acid and extracted with chloroform, followed by crystallization from methanol to give N-(m-iodobenzoyl)-1,3,4,6-tetra-O-acetyl-D-glucosamine (ABGA) (1.50 g).

Workup

  1. customexcessive thionyl chloride was removed by distillation under reduced pressure
  2. dissolutionThe thus prepared m-iodobenzoyl chloride was dissolved in benzene (2 ml)
  3. stirringby stirring for 48 hours
  4. extractionextracted with chloroform
  5. customfollowed by crystallization from methanol

Sources & evidence

ORD record
ord-e2a6f5ca54c547518b5178e2b31a1f0f
Source dataset
uspto-grants-1991_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05034212

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes